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Title: Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct

A β-4-β' C 70 bis-adduct regioisomer and an uncommon mono-adduct β-malonate C 70 derivative were synthesized by using a Diels–Alder cycloaddition followed by an addition–elimination of bromo-ethylmalonate and a retro-Diels–Alder cycloaddition reaction. Here, we also report the regioselective synthesis and spectroscopic characterization of C s-symmetric tris- and C 2v-symmetric tetra-adducts of C 70, which are the precursors of the mono- and bis-adduct final products.
Authors:
 [1] ; ORCiD logo [2] ;  [2] ;  [3] ; ORCiD logo [2]
  1. Univ. of Texas at El Paso, El Paso, TX (United States); Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
  2. Univ. of Texas at El Paso, El Paso, TX (United States)
  3. Florida State Univ., Tallahassee, FL (United States)
Publication Date:
Report Number(s):
LLNL-JRNL-715857
Journal ID: ISSN 0022-3263
Grant/Contract Number:
AC52-07NA27344
Type:
Accepted Manuscript
Journal Name:
Journal of Organic Chemistry
Additional Journal Information:
Journal Volume: 82; Journal Issue: 2; Journal ID: ISSN 0022-3263
Publisher:
American Chemical Society
Research Org:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1347677

Cerón, Maira R., Castro, Edison, Neti, Venkata S. Pavan K., Dunk, Paul W., and Echegoyen, Luis A.. Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct. United States: N. p., Web. doi:10.1021/acs.joc.6b02301.
Cerón, Maira R., Castro, Edison, Neti, Venkata S. Pavan K., Dunk, Paul W., & Echegoyen, Luis A.. Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct. United States. doi:10.1021/acs.joc.6b02301.
Cerón, Maira R., Castro, Edison, Neti, Venkata S. Pavan K., Dunk, Paul W., and Echegoyen, Luis A.. 2016. "Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct". United States. doi:10.1021/acs.joc.6b02301. https://www.osti.gov/servlets/purl/1347677.
@article{osti_1347677,
title = {Regiochemically controlled synthesis of a β-4-β' [70]fullerene bis-adduct},
author = {Cerón, Maira R. and Castro, Edison and Neti, Venkata S. Pavan K. and Dunk, Paul W. and Echegoyen, Luis A.},
abstractNote = {A β-4-β' C70 bis-adduct regioisomer and an uncommon mono-adduct β-malonate C70 derivative were synthesized by using a Diels–Alder cycloaddition followed by an addition–elimination of bromo-ethylmalonate and a retro-Diels–Alder cycloaddition reaction. Here, we also report the regioselective synthesis and spectroscopic characterization of Cs-symmetric tris- and C2v-symmetric tetra-adducts of C70, which are the precursors of the mono- and bis-adduct final products.},
doi = {10.1021/acs.joc.6b02301},
journal = {Journal of Organic Chemistry},
number = 2,
volume = 82,
place = {United States},
year = {2016},
month = {12}
}